Konrad von Jungingen came from the Swabian League and joined the Teutonic Order together with his younger brother Ulrich around 1380.

In the Neumarch, the local knights objected to the dictatorial power of the Order, and a peasant uprising, instigated by Jogaila, broke out in Samogitia.

In 1398, King Albert of Sweden pledged the island of Gotland to the Order in an attempt to curtail the predatory attacks of the Victual Brothers on maritime shipping throughout the Baltic Sea.

That would bring Konrad into conflict with the newly-formed Kalmar Union under Queen Margaret I of Denmark when the Order refused to relinquish Gotland.

According to the Chronicle of Gdańsk, the dying Grand Master warned the Teutonic dignitaries against choosing his militant brother as a successor and called him a fool.